Reduction and Acetylation of 2,4-Dinitrotoluene by a Pseudomonas aeruginosa Strain.

Applied and Environmental Microbiology
D R Noguera, David L Freedman

Abstract

Aerobic and anoxic biotransformation of 2,4-dinitrotoluene (DNT) was examined by using a Pseudomonas aeruginosa strain isolated from a plant treating propellant manufacturing wastewater. DNT biotransformation in the presence and absence of oxygen was mostly reductive and was representative of the type of cometabolic transformations that occur when a high concentration of an easily degradable carbon source is present. P. aeruginosa reduced both nitro groups on DNT, with the formation of mainly 4-amino-2-nitrotoluene and 2-amino-4-nitrotoluene and small quantities of 2,4-diaminotoluene. Acetylation of the arylamines was a significant reaction. 4-Acetamide-2-nitrotoluene and the novel compounds 2-acetamide-4-nitrotoluene, 4-acetamide-2-aminotoluene, and 2,4-diacetamidetoluene were identified as DNT metabolites. The biotransformation of 2,4-diaminotoluene to 4-acetamide-2-aminotoluene was 24 times faster than abiotic transformation. 2-Nitrotoluene and 4-nitrotoluene were also reduced to their corresponding toluidines and then acetylated. However, the yield of 4-acetamidetoluene was much higher than that of 2-acetamidetoluene, demonstrating that acetylation at the position para to the methyl group was favored.

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Citations

Sep 4, 2001·Biotechnology & Genetic Engineering Reviews·C E FrenchN C Bruce
Sep 21, 2011·Journal of Environmental Science and Health. Part A, Toxic/hazardous Substances & Environmental Engineering·Jan PacaEvguenii Kozliak
Apr 26, 2013·Applied Microbiology and Biotechnology·Sharon Yagur-KrollShimshon Belkin
Dec 10, 2017·Applied and Environmental Microbiology·Benjamin ShemerShimshon Belkin
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Aug 10, 2010·Environmental Science & Technology·Damian E HelblingKathrin Fenner
May 1, 2009·Journal of Environmental Sciences (China)·Haizhen WuShizhong Liang

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